Answers revealed in the comments.
GAME 1
In the 1990s, two musical acts replaced themselves at #1 on the Billboard Hot 100. One of those acts is Boyz II Men and other is Puff Daddy. Name either of those artists’ pairs of songs.
GAME 2
“The Winning Team,” “Peace, Experience, Prosperity,” and “In Your Heart, You Know He’s Right,” are presidential campaign slogans used by three consecutive losing presidential candidates. Name any one of those candidates.
hebspeaks 
game one answers:
“I’ll Make Love to You” and “On Bended Knee”
“I’ll Be Missing You” and “Mo Money Mo Problems”
GAME 2 answers:
Adlai Stevenson
Richard Nixon
Barry Goldwater